Synthesis and Biological Evaluation of Hydroxylcoumarin Derivatives as Antioxidant Agents

doi:10.1007/s40242-017-6411-8

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (2): 194-199.doi: 10.1007/s40242-017-6411-8

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Synthesis and Biological Evaluation of Hydroxylcoumarin Derivatives as Antioxidant Agents

CHEN Chen¹, WANG Ping², ZOU Liwei², YANG Ling², FAN Yiming², HU Wenzhong¹, GE Guangbo²

1. College of Life Science, Dalian Minzu University, Dalian 116600, P. R. China;
2. Laboratory of Pharmaceutical Resource Discovery, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China

Received:2016-10-09 Revised:2016-12-28 Online:2017-04-01 Published:2017-02-22
Contact: WANG Ping,E-mail:wangping12@dicp.ac.cn;GE Guangbo,E-mail:geguangbo@dicp.ac.cn E-mail:wangping12@dicp.ac.cn;geguangbo@dicp.ac.cn
Supported by:
Supported by the National Basic Research Program of China(No.2013CB531800), the National Natural Science Foundation of China(Nos.81402822, 81603187, 31471923, 31601517) and the Fundamental Research Funds for the Central Universities of China(No.DC201501020101).

Abstract

Abstract:

In this study, esculetin(1) was chosen as a lead compound and some structural modifications were designed to explore the antioxidant activities of esculetin derivatives. Meanwhile, a convenient method for selective methylation of catechol coumarins with different bases was developed. Furthermore, a few 5,7-dihydroxylcoumarins were synthesized and 7-hydroxylcoumarins were employed in order to explore the potential structure-antioxidant activity relationships. The antioxidant activities of these compounds were evaluated and compared with standard antioxidant Trolox by the 2,2'-diphenyl-1-picrylhydrazyl(DPPH) assay, 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulfonate) cation(ABTS⁺) assay and ferric reducing antioxidant power(FRAP) assay. The results show that the catechol group is the key pharmacophore. Meanwhile, introducing electronegative groups at the C4 position of esculetin(1) may enhance the antioxidative capacity, while introducing a group containing nitrogen as a hydrogen bond acceptor at the C8 position may slightly reduce the antioxidative capacity. Among them, the most powerful antioxidants are compounds 5 and 7, which exhibit higher antioxidant activity than esculetin(1) in all assays.

Key words: Hydroxylcoumarin, Antioxidant activity, Radical scavenging effect, Structure-activity relationship

CHEN Chen, WANG Ping, ZOU Liwei, YANG Ling, FAN Yiming, HU Wenzhong, GE Guangbo. Synthesis and Biological Evaluation of Hydroxylcoumarin Derivatives as Antioxidant Agents[J]. Chemical Research in Chinese Universities, 2017, 33(2): 194-199.

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Synthesis and Biological Evaluation of Hydroxylcoumarin Derivatives as Antioxidant Agents

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